I've always enjoyed cover tunes; there's something compelling about hearing a singer search for personal meaning in someone else's song. Even as a kid, I was quite happy to let Manfred Mann's Earth Band have their way with Springsteen's "Blinded by the Light." While it would be fun to catalog the deliciously erroneous attempts at musical reinterpretation—Barbra Streisand doing Bowie's "Life on Mars," kids?—I'll save that for some other list and offer you eight of what I consider unqualified successes. Many of them are, I think, better than the originals. All of them, I know, are sort of melancholy tales of love and regret:

1. Waits' Cookie-Monster-meets-a-drunken-Louis-Armstrong rumble transforms this West Side Story standard into the last gasp of every disillusioned outcast. Plus, it's a gorgeous arrangement.

2. I know you're not supposed to admit to such things, but I would almost always rather listen to someone else singing Dylan, and Havens' abiding compassion is just right for bringing out Bob's warmth.

3. Nico's ghoulish moan faces Jackson Browne's wistfulness. The result: an ineffably affecting folkie dirge. "Please don't confront me with my failures/I had not forgotten them"? It's like listening to Vampira mourning her lost days in the sun.

4. When tantric followers go on and on about "spiritual sex," I assume they mean something akin to the 6 minutes and 53 seconds of carnal, ethereal devotion with which Buckley embraces Leonard Cohen's classic.

5. Ronstadt and Harris harmonize on this haunting Sinéad O'Connor track from their undervalued Western Wall collaboration.

6. Leon Russell's promise to "love you in a place where there's no space or time" sounds signed in blood after Hathaway sinks his voice into it. It's as crushing, soulful, and smooth as anything Stevie Wonder has ever recorded.

7. A cheat: Mitchell covers Mitchell in a wiser, huskier rerecording from 2000. Yeah, everybody snubs this tune because they're embarrassed by how much their moms dug the Judy Collins version. But the song gets better with age, and so does Mitchell—when she takes a contemplative pause during "I really don't know clouds . . . at all," it squeezes your heart.

8. Simone's improvisational riff on George Harrison is as much proof of her particular genius as her heralded "I Loves You, Porgy" or "Pirate Jenny." She takes an already great song about "how we take each other's love and cause each other pain" and pushes at its borders until it seems to take on vast, visceral new territory. To hear her bemoan that "everything is plas-tic," then wrap up with a quietly appalled "My God," is to know that, yes, indeed, it is a pity.